Acetic Anhydride → HCID 178467255, Verbindung

HRID 1917457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1917457
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[CH:12]=[C:11]([OH:16])[CH2:10]1.[C:17](OC(=O)C)(=[O:19])[CH3:18].CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:10][C:11](=[O:16])[C:12](=[C:17]([OH:19])[CH3:18])[C:13](=[O:15])[CH2:14]1

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 579989705-(2-Bromo-4-fluorophenyl)-3-hydroxycyclohex-2-enone

Produkt 1

HCID 178467255HCID 178467255, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 500 mL recovery flask was added 5-(2-bromo-4-fluorophenyl)-3-hydroxycyclohex-2-enone (1D) (14.3 g, 50.1 mmol, 1.0 eq.), CH2Cl2 (200 mL), acetic anhydride (6.65 g, 65.2 mmol, 1.3 eq.), Et3N (15.22 g, 150 mmol, 3.0 eq.), and DMAP (catalytic amount). The reaction mixture was stirred overnight at room temperature. Monitoring by LC/MS judged the reaction to be complete. The reaction mixture was concentrated and purified via column chromatography (gradient 70% CH2Cl2/Hex to 100% CH2Cl2) to yield the product as light yellow foam which later became an oil (3.55 g, 22%). The crude material was used in the next step without further purification. ESI-MS: m/z 327.2 (M+H)+.

Aufarbeitung

  1. customthe reaction
  2. concentrationThe reaction mixture was concentrated
  3. custompurified via column chromatography (gradient 70% CH2Cl2/Hex to 100% CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-cef37648813a43819634766c15c7403c
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618290B2

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